Gentle Into That Good Night
by elfinblue
Summary: At the end of a surprisingly long life, Sam finally finds his way to Heaven. This story may seem serious, but don't be fooled. It's mostly crack. No slash. No serious pairings, but slight suggestion of Cas/Hannah. Rated T for mildly raunchy humor. One-shot. COMPLETE.


**Author's note: Okay, so here's the deal. I'm WAAAAAYYY the hell behind on my rough draft for my third book, the proofs of my second book are waiting to be checked and returned to the publisher, I have fifteen-gazillion things I need to do to get ready for a convention next month (I'm going to Bouchercon, if you know what Bouchercon is! :D), my car needs work and I'm pretty sure my laundry has piled up to the point that it can be seen in satellite images. So what did I do with my precious day off from my day job today?**

 **This. I did this.**

 **This is pretty much total crackfic, so don't take it too seriously.**

 **WARNINGS: Deathfic. Crackfic. No serious pairings but a tiny little hint of Cas/Hannah.**

 **DISCLAIMER: This can't possibly be my fault. I'm thinking Rowena cast a spell on me or something.**

Gentle Into That Good Night

by elfinblue

Sam Winchester lived to be much older than he had ever imagined possible.

He aged gracefully and as the world changed and the Winchesters' roles in its continued survival became common knowledge, he became a familiar figure on the nightly news and in the halls of power. He remained tall and imposing, not bowing with age, a tall, stately old man with a shock of white hair. When he drove by in the gleaming Impala (already destined for the Smithsonian when he no longer needed her) crowds waved and cheered and ran behind the car. When he spoke to congress, even the most blowhard politicians listened to him respectfully. And when, at last, it was his time to retreat forever into the eternal night, heads of state and religious leaders from around the world descended on the Men of Letters headquarters to pay their respects and the field where they held his funeral pyre was a media circus.

Sam in spirit, young once more, turned to find a familiar presence at his side.

"Cas! Hey! It's good to see you again!" Sam looked around, but Cas was alone.

"And it's good to see you." Cas surveyed the crowd. "You've done well with your life. I'm sorry I haven't been around more. There have been a lot of changes in Heaven since you were there last and I've been very busy helping with the re-building."

"What kind of changes?"

"Well, every soul still has its own private heaven, except in rare circumstances where two souls share a heaven. But now there are communal areas where souls can mingle, and it's easier for people to visit their loved ones and even meet new people."

"That sounds great."

"It's proven very popular."

The crowds around them faded away. The field lingered for a moment, like smoke from the pyre, then it too was gone and Sam and Cas were standing in a parking lot that had, once upon a time, been a familiar place.

"It's the Road House!" Sam said. It was night here. The windows were lighted and the sound of music and laughter came from within.

"There are many people here who will be glad to see you," Cas said.

"Do they know I'm here?"

"I doubt it. Time, in Heaven, does not pass in a normal manner. As Shakespeare said, 'time in heaven is a lazy thing, drifting by like the endless days of a childhood summer, or silent flakes of January snow.'"

Sam blinked. "I don't remember Shakespeare saying that."

"Well, he didn't say it until after he was dead."

"Oh."

"I'll not go in with you," Cas said. "Not all of the people here know me and some of them are uncomfortable in the presence of angels. If you need anything, just call me and I will come."

"You just going to hang around out here in the parking lot?"

"No. I'm going to go help Hannah."

"Hannah?"

"Yes. You remember Hannah? She's my...friend."

"Oh. Your...friend."

"Yes. My...friend."

"Well, all right then."

Man and angel embraced and then Cas was gone and Sam turned for the door, his heart light and his step eager.

When he first opened the door, no one in the crowded room looked up. He stood there in the doorway for a moment, taking in the familiar faces.

His mother and Jess-his own, sweet, long-lost Jess-were laughing together at a table near the window. Bobby and Rufus were crowded at the bar with at least a dozen other men and women. Some he recognized and some he did not, but all had the rugged look of hunters. Ellen Harvelle presided behind the bar and he could see, through the pass-through to the kitchen, Karen Singer and, of all beings, Benny Lafitte moving around. Ash and Charlie Bradbury were seated cross-legged on top of the pool table, facing each other, with computers on their laps and VR helmets on their heads, deeply engrossed in some kind of game.

The one person he was most anxious to be reunited with, however, didn't seem to be present.

"Dean's not here!"

It had been decades since Sam had heard a telephone receiver slammed down on the hook, but he still recognized it at once. He followed the sounds and found Jo Harvelle leaning against the wall with her arms crossed over her chest and an angry look on her face.

"Do I look like his freaking secretary?" She demanded of the room at large.

A young man approached her and Sam recognized, with surprised delight, his younger half-brother, Adam Milligan. There was a juke box near the wall telephone and Adam leaned against it in what he probably thought was a cool pose.

"You know, sweetheart," he said, "Dean is never going to see you as anything but a little sister. But if you'd just stop hopelessly crushing on him, you'd realize that there are," he popped his collar, "other Winchester men in the place who'd be more than happy to show a pretty girl like you a good time."

Sam mentally face-palmed.

"Oh, please," Jo said scathingly. "You share a heaven with your mom."

"So? You share a heaven with _your_ mom."

"Of course I do. My mom and I are a couple of badass chicks who went down fighting the good fight in a showdown with Lucifer himself!"

"Well...you still share a heaven with your mom."

"At least our heaven has a bar in it," Jo said. She glanced up then. "Sam!" With a happy shriek she dashed across the room and leaped at him.

Sam hugged her back and suddenly he was in the middle of a crowd of long-lost friends and family members, being eagerly welcomed into Heaven. Charlie and Ash were still lost in their computer game, but everyone else thronged around and it seemed that even those he didn't know, or didn't know well, had something to say.

"Boy, it's good to finally see you, ya idjit!"

Sam returned the fierce embrace. "It's good to see you, too, Bobby!"

Benny was hanging back on the edge of the group and Sam pushed through and offered him his hand.

"Surprised to see me?" the former vampire asked.

"Honestly, yeah. What happened?"

"Tell the truth, I don't rightly know. After you made it through the portal, the other vamps ripped me to shreds. I died in Purgatory as a vampire and woke up here as a human. A dead human, granted, but still a big ol' improvement."

"And," Ellen put in, "he's the best short-order cook I've ever met!"

Adam got within reach and Sam dragged him in for a hug. "Adam! This is amazing! How is it possible that you're even here?"

"Why? Where else would I be?"

"Well...we thought, when Michael jumped into the cage with Lucifer, that you were still in his body."

"Oh. No, Michael sent me to my mom's heaven before he went to the cemetery for the showdown. That was what he promised me, if I'd let him use my body for the Apocalypse."

"You mean to tell me," Bobby Singer said, "that you were willing to let the whole world burn just so you could see your mother again?"

"Momma's boy," Jo singsonged softly.

"My son is very devoted. There's nothing wrong with that," a woman Sam recognized from her pictures as Kate Milligan said firmly.

"So, wait," Adam said. "This whole time you've thought I was burning in a cage in the pit of Hell?"

"Well...yeah?"

"Wow! You and Dean must have been going out of your minds with guilt and worry!"

"Oh...absolutely!"

Adam peered at Sam suspiciously. "You forgot about me, didn't you?"

"What? No! No. No, certainly not. Never." Adam continued to glare and Sam shifted uncomfortably. "We were going to rescue you?"

"How? And when?"

"...hadn't quite worked that out yet. But we were definitely talking about it."

Mary Winchester rescued him.

"Sammy! Sweetie! Come over here and let me look at you! Oh, my baby! You got so big!"

Sam wrapped his mother in his arms and gave her the hug he'd been wanting all his life to give her, and then he was being pulled away again and hugging another blue-eyed blonde woman.

"Jess! Oh, Jess! I've missed you so much!"

"And I've missed you! Sit down, Sam! Sit down and talk to me! There are so many things I've been waiting to say to you!"

Sam dropped into a chair across from her and she reached over the table, took his big hand in both of her small ones, and said, "Sam, honey, I just want you to know that Madison was a sweet girl. What happened to her wasn't her fault and, even though it had only been a few months since I died horribly because you weren't honest with me, I don't blame you for getting involved with her."

"Oh. I-uh-that's...that's really understanding of you."

"Yes. I know." She smiled sweetly. "Now explain to me about Ruby and the fox-demon and that freaking married veterinarian!"

"Uh...uh...I...uh..."

Karen Singer came over, set a hot pie down on the table, and dropped into a chair. "Now, Jess, honey," she said, "you can't really blame Sam for those things."

"Right!" Sam agreed.

"After all, he was practically raised by Bobby Singer!"

"What did I do?" Bobby squawked.

"Oh, that's a good question!" his wife answered. "We never did know exactly what she was, did we? Just some _thing_ that slithered out of Purgatory and into your bed!"

"Listen!" Bobby said angrily, his voice rising over the other noises in the room, "I thought it was human when I had sex with it!"

Ellen chuckled. "Funny how many men in this room could say that...what are you nodding about, Bill Harvelle?"

"Just agreeing with you dear! That's all! Just agreeing!"

"I think Karen's point," Mary said, "is that it's not just Sam. Without us around to guide them, all our men tended to make poor choices about who and what to sleep with." She shot a venomous glare past Sam's shoulder. He shuddered and glanced behind him to find Kate Milligan glaring back.

"Yeah, I don't think I want to be sitting between these two," he muttered.

Kate came over. "So, Mary," she said with mock sweetness, "this is your younger son, is it? This is the one who was demonic first, am I right?"

"Sam's the one who got a full ride to Stanford. What school was your boy in again? A community college, wasn't it?"

"You know perfectly well Adam was studying medicine. He was going to be a doctor. Why, I do believe he was on the honor roll almost as often as your sons were on the Most Wanted List."

"But he still didn't make the honor roll as many times as my boys saved the world."

"MY son was the vessel for the Archangel Michael!"

"MY sons defied Heaven and Hell to save humanity!"

"MY son was a straight-A student!"

"MY sons rebuilt the Men of Letters!"

"MY son died a virgin!"

"MOM!" Adam yelped. "COULD YOU NOT?"

"I knew it," Jo said.

"I think we're done here, Baby," Kate said. "If my son's father returns, please tell him that I'd like to speak with him."

"Did everyone hear that?" Mary called out. "If anyone happens to see MY HUSBAND, tell him that his one-night-stand is looking for him."

"So...Dad's not here?" Sam asked Bobby.

"Here? Here in the same room with his wife and girlfriend?" Bobby snorted. "John Winchester's a lot of things, boy, but stupid ain't one of 'em."

"And what about Dean?" Sam was practically whining now. "Where's Dean?"

The phone rang on the wall. Jo picked it up.

"Harvelle's Road House...No! Dean Winchester isn't here! No, I'm not gonna take a message! Stop calling here!"

She slammed the receiver down.

"Who was it this time?" her mother asked.

"Marilyn Freaking Monroe! Again! I swear, she's almost as bad as Jean Harlow!"

"So," Sam said slowly, "Marilyn Monroe and Jean Harlow are looking for Dean? _The_ Marilyn Monroe and Jean Harlow?"

"Oh, that's just the tip of the iceberg," Jo stormed. "Marilyn, Jean, Farrah, Rita Heyworth, Billie Holliday, Betty White..."

Sam snickered. "Betty White?"

"Don't knock it 'til you've seen her young again," Bobby advised. "Betty White is hot!" He caught the look Karen was giving him. "Er, uh, that's what Dean says, anyway."

"But where's Dean?"

"Dean's on a hunting trip and he hasn't been home in a few days. Why don't you ask Cas? Maybe he knows where to find him."

Sam stepped back out into the Heavenly night, paced a few steps from the building and called Cas in his mind.

The angel appeared at once. "Yes, Sam? Did you need something?"

"Dean's not here. Do you know where he is?"

"Did you check with Marilyn Monroe?"

"He's not there. Bobby said he went on a hunting trip?"

"Oh." Cas looked up at the sky and spoke, but not to Sam. "Does anyone know where Dean Winchester has gotten to now? He did? He is? Are you sure? Thank you." He turned his attention back to the younger Winchester. "I'm told that he's in Michael's heaven."

"Michael's heaven? The Archangel Michael? He's not in the cage anymore?"

"Not that Michael." Cas put two fingers on Sam's forehead and suddenly Sam found himself in a lush, tropical jungle. He turned in an almost complete circle before he was suddenly wrapped in a fierce bearhug and tackled into the undergrowth.

"Dean!" Sam choked out, and found that he was crying. "Dean! God! I've missed you so much!"

"I've missed you too," his big brother hissed in his ear. "Now shut the hell up and don't move or it'll hear you."

"What'll hear me?" he whispered back.

"Shh!"

The ground trembled beneath them and something enormous snuffled and snorted nearby.

"Don't move," Dean breathed in Sam's ear. "Seriously. Don't move. Its eyesight is crap but its hearing is incredible. Also, it rocks at sensing movement."

Sam's eyes narrowed in the darkness. "Michael's heaven," he repeated. "Michael...Crichton? Dean, are we in Jurassic Park? Are you hunting a T-Rex?"

"What? Me? Hunting a T-Rex? Don't be ridiculous," Dean scoffed.

"Good."

"I'm hunting the velociraptors. The T-Rex is just being a drama queen about it."

A massive, clawed, reptilian foot came down just outside their hiding place and a head the size of a Volkswagen snuffled by. The brothers remained perfectly still and after a few breathless minutes the monster wandered away.

"Here," Dean said. "Let's go outside where we can talk without worrying about being eaten."

"Always a good idea," Sam agreed.

Dean brushed aside some of the leaves to reveal a manhole cover in the middle of the jungle. He lifted it easily and they climbed through. Sam closed the cover behind them and they were standing beside the Impala on a moonlit road.

"And did Michael Crichton know you were in his heaven, hunting his velociraptors?"

"Um...well, not in so many words, no. He wouldn't have minded, though. Really! He's totally cool. Now Lovecraft, he gets pissed when you sneak in and take out Cthulu! Anyway, there's gonna be a really awesome hunt coming up in a while. Now that you're here, it will be totally cool! Hey! And maybe we can get Dad and Bobby to come hunting with us."

"What kind of hunt?"

"I don't know yet. Some of my friends are writing it for me."

"They're writing you a hunt. What friends?"

"Well, ah, Terry Pratchett, and Alfred Hitchcock, and Wes Craven, and Mary Shelley. It's taking them awhile to work out all the details, though."

"So this is what you've been doing while I've been down on Earth working my tail off?" Sam asked. "Dating starlets and hunting mythical creatures?"

"Not just starlets."

Sam laughed ruefully. "I don't believe you. Except that I do. This is so you." He thought about Jess' grievances, and Karen's and his mother's. "I can just imagine some of the hoops you must have to jump through to keep out of trouble with all those women."

"What trouble? I'm never in any trouble."

"How can you not be?"

"Simple. I never lied to any of them or promised them anything I couldn't give them."

"Mmm." Sam considered that and supposed it was true. "Jo's not to happy with you."

"Jo," Dean said. "Man, I can't date Jo. She's like a sister. Besides, Ellen would kill me."

"You're already dead, Dean."

"You think that'd stop her?"

Sam laughed. "Now that you mention it, no, probably not."

Dean, jingling his keys in way Sam had sorely missed without even realizing it, circled the Impala and slid behind the wheel. Sam got in the passenger side and they sat there in companionable silence for a long moment.

"So what now?" Dean asked. "What do you want to do, Sammy?"

"What do you mean?"

"What do I mean? What do you think I mean? We're in Heaven. You can do anything you want to. Nothing's off the table. You want to marry Jess and settle down in a nice little house with a white picket fence and a dog, you can do that. Go back to school? They got schools here like you never dreamed of. Study under Plato or Socrates or argue case law with Lincoln or Darrow. Learn science from Newton and Einstein and Galileo. Whatever you want, Sammy. Anything you want to do."

Sam considered.

"You know what I really want to do?" he asked.

Dean shook his head a little, frowned, his lips pushed out in a little pout. "No. What?"

Sam looked over at him and their eyes met. Sam grinned.

"I want to go on a road trip with my brother."

Dean froze, cleared his throat. His eyes glinted in the starlight.

"Really?"

"Yeah. Really."

Dean relaxed, sat up a little straighter and half smiled. "Well, a'right then. What are we waiting for?"

In unison, the two men reached for their door handles and slammed the car doors. Dean started the engine and it echoed down the dark road and shivered the leaves on the trees that arched overhead. He shifted it into gear and drove away, the taillights fading into the distance, the sound of music trailing behind them.

 _"Carry on my wayward sons._

 _There'll be peace when you are done._

 _Lay your weary heads to rest._

 _Don't you cry no more."_


End file.
